diff --git a/spec/operators/retryWhen-spec.ts b/spec/operators/retryWhen-spec.ts
index d145d6e4c0..227a595919 100644
--- a/spec/operators/retryWhen-spec.ts
+++ b/spec/operators/retryWhen-spec.ts
@@ -1,7 +1,7 @@
 import { expect } from 'chai';
 import { hot, cold, expectObservable, expectSubscriptions } from '../helpers/marble-testing';
 import { retryWhen, map, mergeMap, takeUntil } from 'rxjs/operators';
-import { of, EMPTY } from 'rxjs';
+import { of, EMPTY, Observable, throwError } from 'rxjs';
 
 /** @test {retryWhen} */
 describe('retryWhen operator', () => {
@@ -329,4 +329,25 @@ describe('retryWhen operator', () => {
     expectObservable(result).toBe(expected);
     expectSubscriptions(source.subscriptions).toBe(subs);
   });
+
+  it('should always teardown before starting the next cycle, even when synchronous', () => {
+    const results: any[] = [];
+    const source = new Observable<number>(subscriber => {
+      subscriber.next(1);
+      subscriber.next(2);
+      subscriber.error('bad');
+      return () => {
+        results.push('teardown');
+      }
+    });
+    const subscription = source.pipe(retryWhen(errors$ => errors$.pipe(
+      mergeMap((err, i) => i < 3 ? of(true) : throwError(err))
+    ))).subscribe({
+      next: value => results.push(value),
+      error: (err) => results.push(err)
+    });
+
+    expect(subscription.closed).to.be.true;
+    expect(results).to.deep.equal([1, 2, 'teardown', 1, 2, 'teardown', 1, 2, 'teardown', 1, 2, 'bad', 'teardown'])
+  });
 });
diff --git a/src/internal/operators/retryWhen.ts b/src/internal/operators/retryWhen.ts
index 5368ea8611..c5d1d05626 100644
--- a/src/internal/operators/retryWhen.ts
+++ b/src/internal/operators/retryWhen.ts
@@ -1,13 +1,11 @@
-import { Operator } from '../Operator';
+/** @prettier */
 import { Subscriber } from '../Subscriber';
 import { Observable } from '../Observable';
 import { Subject } from '../Subject';
 import { Subscription } from '../Subscription';
 
-
-import { MonoTypeOperatorFunction, TeardownLogic } from '../types';
+import { MonoTypeOperatorFunction } from '../types';
 import { lift } from '../util/lift';
-import { SimpleOuterSubscriber, innerSubscribe, SimpleInnerSubscriber } from '../innerSubscribe';
 
 /**
  * Returns an Observable that mirrors the source Observable with the exception of an `error`. If the source Observable
@@ -62,88 +60,84 @@ import { SimpleOuterSubscriber, innerSubscribe, SimpleInnerSubscriber } from '..
  * @name retryWhen
  */
 export function retryWhen<T>(notifier: (errors: Observable<any>) => Observable<any>): MonoTypeOperatorFunction<T> {
-  return (source: Observable<T>) => lift(source, new RetryWhenOperator(notifier, source));
-}
-
-class RetryWhenOperator<T> implements Operator<T, T> {
-  constructor(protected notifier: (errors: Observable<any>) => Observable<any>,
-              protected source: Observable<T>) {
-  }
-
-  call(subscriber: Subscriber<T>, source: any): TeardownLogic {
-    return source.subscribe(new RetryWhenSubscriber(subscriber, this.notifier, this.source));
-  }
-}
-
-/**
- * We need this JSDoc comment for affecting ESDoc.
- * @ignore
- * @extends {Ignored}
- */
-class RetryWhenSubscriber<T, R> extends SimpleOuterSubscriber<T, R> {
-
-  private errors: Subject<any> | null = null;
-  private retries: Observable<any> | null = null;
-  private retriesSubscription: Subscription | null | undefined = null;
-
-  constructor(destination: Subscriber<R>,
-              private notifier: (errors: Observable<any>) => Observable<any>,
-              private source: Observable<T>) {
-    super(destination);
-  }
-
-  error(err: any) {
-    if (!this.isStopped) {
-
-      let errors = this.errors;
-      let retries = this.retries;
-      let retriesSubscription = this.retriesSubscription;
-
-      if (!retries) {
-        errors = new Subject();
-        try {
-          const { notifier } = this;
-          retries = notifier(errors);
-        } catch (e) {
-          return super.error(e);
+  return (source: Observable<T>) =>
+    lift(source, function (this: Subscriber<T>, source: Observable<T>) {
+      const subscriber = this;
+      const subscription = new Subscription();
+      let innerSub: Subscription | null;
+      let syncResub = false;
+      let errors$: Subject<any>;
+
+      /**
+       * Gets the subject to send errors through. If it doesn't exist,
+       * we know we need to setup the notifier.
+       */
+      const getErrorSubject = () => {
+        if (!errors$) {
+          errors$ = new Subject();
+          let notifier$: Observable<any>;
+          // The notifier is a user-provided function, so we need to do
+          // some error handling.
+          try {
+            notifier$ = notifier(errors$);
+          } catch (err) {
+            subscriber.error(err);
+            // Returning null here will cause the code below to
+            // notice there's been a problem and skip error notification.
+            return null;
+          }
+          subscription.add(
+            notifier$.subscribe({
+              next: () => {
+                if (innerSub) {
+                  subscribeNext();
+                } else {
+                  // If we don't have an innerSub yet, that's because the inner subscription
+                  // call hasn't even returned yet. We've arrived here synchronously.
+                  // So we flag that we want to resub, such that we can ensure teardown
+                  // happens before we resubscribe.
+                  syncResub = true;
+                }
+              },
+              error: (err) => subscriber.error(err),
+              complete: () => subscriber.complete(),
+            })
+          );
         }
-        retriesSubscription = innerSubscribe(retries, new SimpleInnerSubscriber(this));
-      } else {
-        this.errors = null;
-        this.retriesSubscription = null;
-      }
-
-      this._unsubscribeAndRecycle();
-
-      this.errors = errors;
-      this.retries = retries;
-      this.retriesSubscription = retriesSubscription;
-
-      errors!.next(err);
-    }
-  }
-
-  /** @deprecated This is an internal implementation detail, do not use. */
-  _unsubscribe() {
-    const { errors, retriesSubscription } = this;
-    if (errors) {
-      errors.unsubscribe();
-      this.errors = null;
-    }
-    if (retriesSubscription) {
-      retriesSubscription.unsubscribe();
-      this.retriesSubscription = null;
-    }
-    this.retries = null;
-  }
-
-  notifyNext(): void {
-    const { _unsubscribe } = this;
+        return errors$;
+      };
+
+      const subscribeNext = () => {
+        innerSub = source.subscribe({
+          next: (value) => subscriber.next(value),
+          error: (err) => {
+            const errors$ = getErrorSubject();
+            if (errors$) {
+              // We have set up the notifier without error.
+              errors$.next(err);
+            }
+          },
+          complete: () => subscriber.complete(),
+        });
+        if (syncResub) {
+          // Ensure that the inner subscription is torn down before
+          // moving on to the next subscription in the synchronous case.
+          // If we don't do this here, all inner subscriptions will not be
+          // torn down until the entire observable is done.
+          innerSub.unsubscribe();
+          innerSub = null;
+          // We may need to do this multiple times, so reset the flag.
+          syncResub = false;
+          // Resubscribe
+          subscribeNext();
+        } else {
+          subscription.add(innerSub);
+        }
+      };
 
-    this._unsubscribe = null!;
-    this._unsubscribeAndRecycle();
-    this._unsubscribe = _unsubscribe;
+      // Start the subscription
+      subscribeNext();
 
-    this.source.subscribe(this);
-  }
+      return subscription;
+    });
 }